Express Session Undefined

So I'm using middleware to combine the express.js and socket.io sessions (see [this question]). I have implemented it before in a previous version of my code, but I'm struggling now.

login.js

if (bool) { 
    //create session, return success status
    req.session.loggedIn = true;
    console.log("Setting login", req.session.loggedIn); //logs true
    req.session.user = user[0].id;
    req.session.player = new Player(user[0].id, user[0].username);
    response.msg = "You have logged in!";
    response.flag = false;
    console.log(req.sessionID); //logs session id
}

Now if we go to my server, I have it setup with:

const sessionMiddleware = session({
    secret: 'keyboard cat',
    resave: false,
    saveUninitialized: true,
    cookie: {secure:false}
});

//create the server
const server = app.listen(8080, () => {
    const port = server.address().port;
    console.log(`SourceUndead has risen from the grave on port ${port}`);
});

//attach socket to process
const io = socket.listen(server);

//APPLY THAT SESSION BRAH
io.use(function(socket, next) {
    sessionMiddleware(socket.request, socket.request.res, next);
});

app.use(sessionMiddleware);

Now, when I log in, it should set my req.session variables, and they do log inside login.js, but the session isn't being saved because if I reload the page, it should redirect you to the index page (done by react polling the API). I know that in post routes, the session is only saved if you define req.session.save() if you don't use res.send() or a variation. I have tried both.

My server output:

Socket connection NeqQpiNB1BdskTUS7Wd9L19RXu-r20u8
Is logged in undefined
Setting login true
TcC0OVpZuBVFqxEL1bgW9x9zxtXwcGb6
Socket connection Q3S8mSfPWDiAlo54QloyGBGGWHV8hchD
Is logged in undefined

How do I get my session variables to persist on my server?

via Sterling Archer